Adenylic acid structure

FIGURE 11.13 Structures of the four cotntnou ribonucleotides—AMP, GMP, CMP, and UMP—together with their two sets of full uatnes, for example, adeuosiue 5 -mouophosphate and adenylic acid. Also shown is the nucleoside 3 -AMP. 

The bearing which these discoveries have had on the elucidation of the structure of ribopolynucleotides will be discussed later. It is important to stress here, however, that, for most purposes, the older methods of preparing nucleotides have been superseded by procedures which yield separate isomers of each. Of the techniques mentioned above, paper chromatography iB mainly of analytical value, and is the most convenient method for the qualitative detection of isomeric adenylic acids. The only disadvantage of this method is that the isomers are not completely separable from muscle adenylic acid. The presence of the latter, however, can be readily detected by hydrolyzing it to adenosine by means of the specific 5-nucleotidase present in snake venoms,66 or by deamination by a specific enzyme... 

Structure and Function of Peptidyl Carrier Protein Domains Structure and Function of Adenylation Domains Structure and Function of Condensation Domains Structure and Function of Thioesterase Domains Multidomain NRPS Structural Information PCP-C didomain structure PCP-TE didomain structure Structure of a C-A-PCP-TE termination module Pathways to Nonproteinogenic Amino Acids Incorporated into NRP Natural Nonproteinogenic Amino Acids Present as Cellular Metabolites Modification of Proteinogenic Amino Acids Nonproteinogenic Amino Acids Derived from Multistep Pathways Tailoring Enzymology in NRP Natural Products Chemical Approaches Toward Mechanistic Probes and Inhibitors of NRPS... 

ADENINE. [CAS 73-24-5]. A prominent member of the family of naturally occurring purines (see Structure 1). Adenine occurs not only in ribonucleic adds (RNA), and deoxyribonucleic acids (DNA). but in nucleosides, such as adenosine, and nucleotides, such as adenylic acid, which may be linked with enzymatic functions quite apart from nucleic adds. Adenine, in the form of its ribonucleotide, is produced in mammals and fowls endogenously from smaller molecules and no nutritional essentiality is ascribed to it. In the nucleosides, nucleotides, and nucleic acids, the attachment or the sugar moiety is at position 9. 

The structure of firefly luciferin has been confirmed by total synthesis. The firefly emits a ycllow-grccn luminescence, and luciferin in this case is a benzthiazole derivative. Activation of the firefly luciferin involves the elimination of pyrophosphate from ATP widi the formation of an add anhydride linkage between the carboxyl group of luciferin and the phosphate group of adenylic acid forming luciferyl-adenylate. 

This K is considerably smaller than that of the single-strand polymer at neutral pH, and suggests that the molecules have a rather thick structure. Adopting the interrupted-helix model, we may apply Eq. (97) as in the case of poly-L-proline. Noting that the unit translation distance b0 is 1.70 A for the double-stranded Watson-Crick helix (263 ) [i. e., a distance of 3.40 A for two residues, one in each chain], and taking Mu = 328 for poly(adenylic acid), we obtain r = 22 residues per helical... 

Fig. 17.2. Chemical structures of some nucleotides adenosine-5 -phosphate or 5 -adenylic acid adenosine-3 -phosphate or 3 -adenylic acid adenosine-3, S -disphosphate...

In confirmation of this structure, Klimek and Parnas found that muscle adenylic acid forms a complex with boric acid. Such a complex has been shown by Boeseken to be formed only by polyhydroxy compounds having two adjacent ds hydroxyl groups. 

Nucleic acids, the compounds that control heredity on the molecular level, are polymers composed of nucleotide units. The structures of nucleotides have been determined in the following way, as illustrated for adenylic acid, a nucleotide isolated from yeast cells. 

Recent primary structure sequence studies on Escherichia colt glutamine synthetase demonstrated that the covalently bound active site adenylic acid residue is attached to a tyrosine residue (235). The sequence of amino acids around the derivated tyrosine residue is ... 

Adenylic Acid. Adenosine 3 -monophosphate adenosine - 3 -phosphoric acid adenosine - 3 -monophos-phoric acid adenylic acid b yeast adenylic acid synadenylic acid h-adenylic acid. C HuNjOyP mol wt 347.23. C 34.59%, H 4.06%, N 20.17%, O 32.26%, P 8.92%. Early prepns from yeast nucleic acid Levene. Bass, Nucleic Acids, (Chemical Catalogue Co., New York, 1931). Early work probebty done on mixtures of 2 - and 3 -adenylic acids both compds isomerize readily to form an equilibrium mix -Hire under acid conditions Carter, Cohn, Fed. Proc. 8, 190 (1949) Baddily, in The Nucleic Acids vol. 1, E. Chargaff, J. N. Davidson, Eds. (Academic Press, New Yotk, 1955) pp 165-168 A. M. Michelson, The Chemistry of Nucleoside and Nucleotides (Academic Press, New York, 1963) pp 100-106. Synthesis Brnwn, Todd, J. Chem. Soc. 1952, 44. Structure nf dihydrate Brown el at, Nature 172, 1184... 

Adenylic Acid. Muscle adenylic acid ergaden -ylic acid t -adenylic acid adenosine S -monophosphate adenosine phosphate adenosine-5 -phosphoric add edeno-sine-5. monophosphoric acid A5MP AMP NSC-20264 Addiyl Cardiomone (Na salt) Lycedan My -B-Den My-oston Phosaden. C,0HhNjO7P mol wt 347.23, C 34.59%, H 4.06%, N 20.17%, O 32,25%, P 8,92%. Nucleotide widely distributed in nature. Prepn from tissues Embden, Zimmerman, Z. Physrot Chem. 167, 137 (1927) Embden, Schmidt, ibid. 181, 130 (1929) cf. Kalckar, J. B.ol Chem. 167, 445 (1947). Prepn by hydrolysis of ATP with barium hydroxide Kerr, 3. Biot Chem. 139, 13l (1941). Synthesis Baddiley, Todd. 3. Chem. Soc. 1947, 648. Commercial prepn by enzymatic phosphorylation of adenosine. Monograph on synthesis of nucleotides G. R. Pettit. Synthetic Nucleotides vol, 1 (Van Nostrand-Reinhold. New York, 1972) 252 pp. Crystal structure Kraut, lensen, Acta Cryst 16, 79 (1963). Reviews see Adenosine Nucleic Acids. 

Japan, pat. 732C86) (to Ajinomoto), C.A. 51, 3870b (1957). Structure Levene, Bess, op. ctt.. pp 187-192 Bredereck, Ber. 66, 198 (1933) Levene, Tipson, J. Biol. Chem. Ill, 3t3 (1935). Also prepd from muscle by enzymatic deamination of muscle adenylic acid Ostem, Biochem. Z. 254, 63 (1932) by hydrolysis of inosine triphosphate Kleinzeller, Biochem. J. 36, 729 (1942). Studies on the enzymatic synthesis Greenberg, J. Biol. Chem. 198, 611 (1951) Korn et al, ibid 217, 875 (1955). Microbial fermentation method using mutant strains of Micrococcus glutamicus Kinoshita el al. U.S. pat. 3,232,844 (1966 to Kyowa). 

To eliminate some of the present ambiguity concerning these structures, we have examined the behavior of a number of oligomers and the polymer of adenylic acid, as well as the polymer of A6-hydroxyethyladenylic acid (poly HEA). We have been concerned with both the explanation of their optical properties in terms of proposed models and the thermodynamics of the melting process. It is hoped that the information so obtained will help to clarify the importance of order-disorder phenomena in biology and questions concerning the structure of such biologically important polynucleotides as RNA. 

Nuclear magnetic resonance analysis with double and triple resonance was used to elucidate the structure as 3, 4 -dideoxykanamycin B 2"-adenylate. The spectrum of the inactivated 3, 4 -dideoxykanamycin B in deuterium oxide at pH 8.0, with tetramethylsilane as the external reference standard (8 =0), showed signals at 8 8.63 and 8.85 attributable to the adenine-ring protons, and at 8 6.53, 5.28, 4.98, 4.83 and 4.6 (H-2) the latter were assigned to the D-ribose-ring protons by successive doubleresonance experiments, and by comparison with disodium 5 -adenylate in deuterium oxide. Therefore, these observations confirmed the presence of one molecular proportion of 5 -adenylic acid in the molecule. Irradiation at 8 5.45 (7 3.6, H-1") caused the complex signal at 8 4.3 (H-2")... 

---